


Propriety Amiss

by kittenofdoomage



Category: Supernatural
Genre: Dry Humping, F/M, NSFW, Reader Insert, Sex, Smut
Language: English
Status: Completed
Published: 2016-02-01
Updated: 2016-02-01
Packaged: 2018-05-17 17:08:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,571
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5878885
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: <blockquote class="userstuff">
              <p>Summary: Left to babysit the Winchester's grandfather when he's misplaced in time, the reader finds herself attracted to him.</p>
            </blockquote>





	Propriety Amiss

‘He’s your grandfather?’ You blinked at Dean’s explanation, looking over at the clean cut guy in the suit, who looked like he’d fallen straight out of a cheery fifties musical. Henry Winchester, for his part, gave a tight grin and waved a little. At least he displayed some of the classic Winchester social awkwardness. Unless these guys were in fed-mode, they were pretty useless with the general human poplace.

'Yeah.’ Sam confirmed, moving over to the bed. 'And he’s got a pretty nasty demon on his tail, so we need to shift it.’

'Demon?’ You questioned.

'Her name…well, she’s not technically female I suppose as she’s…’ Three sets of eyes landed on the misplaced Winchester and he went a little red. 'It doesn’t matter. She’s called Abaddon and she’s as evil as they come.’

You nodded, watching as the boys packed up their gear quickly, years of running from danger and avoiding the enemy making them one slick unit. Your own bag was still in your car, having rushed from the other motel when they had called you. As they finished putting their stuff into the worn duffel bags, they stood straight. 'Right.’ Dean pointed at Henry. 'You’re with her. Two cars, two teams. We’re heading…where are we heading?’

'The place where I was, or was going to be, initiated.’ Henry indicated, giving Dean the address. The eldest brother nodded, looking over at you.

'Keep up, okay.’

You nodded, a little confused as to why Dean was making Henry travel with you. As you followed them outside, heading for your car, you noticed the broken window of the Impala, and frowned, looking over at Henry. 'Did you do that?’ He nodded, a little abashed. And you had your answer.

Nobody hurt baby and then got to sit in her. It was a rule that had been broken over the years many times, but obviously Dean was uncomfortable with the sudden appearance of a stranger claiming to be his grandfather.

Twenty minutes into the journey, and Henry cleared his throat, breaking the uncomfortable silence.

'You’re a hunter too, then?’

'Yeah.’ You replied, keeping your eyes on the rear lights of the Impala ahead of you. 'For a long time.’

'And you work with Dean and Sam.’ He stated, and you shrugged.

'We help each other out.’

Henry nodded, looking over at you. You didn’t return the glance but you could feel his eyes on your. His hands fiddled with the fold in his pants, and you felt a crooked smile pull at your lips. He was terribly adorkable.

'It is curious why a woman would follow such a path.’ He muttered. 'But I suppose, Josie was following a similar choice in life.’

'Josie?’ You asked. 'That your wife?’

'Oh no.’ Henry shook his head. 'John’s mother was called Maisie. She was…not like Josie. Or you. She had no knowledge of the life I led.’

'So she just stayed at home. Like, stepford wife?’

Henry frowned. 'I don’t quite follow.’

You waved a hand, looking over at him briefly. 'Never mind.’ Silence fell over the car like a thick blanket once more, before Henry spoke again.

'I wonder what would have happened if I hadn’t have left.’ He sighed. 'Dean suggested that going back in time to fix this mess would be a bad idea.’

'Clearly. You could change the whole of history. Little bugs and all.’ You shook your head. 'Better you stay here and help us kill Abaddon. I know it’s tough not being able to go back to your wife and kid but…Dean and Sam might not exist at all if you did that.’ You smiled at him, reaching over to tap his knee in comfort. 'Not offence, but I’m rather attached to them.’

Henry smiled. 'I think you and he are both correct. Having had time to think it over…changing the course of history may not be a good idea. Things have happened as they should have.’ He looked out of the window. 'It is a shame that it had to be this way.’

You shrugged. 'Dean and Sam are good men. Two of the bravest, most selfless people I’ve ever met. Maybe life could be better, but the same could be said of many things.’

'You are totally correct.’ You looked over, your eyes meeting Henry’s. You liked this man; his sharply dressed image, his proper speech. He was a real gentleman. Pity not many of them existed nowadays. 'I wonder how Maisie fared after I left.’ He thought aloud. 'She was an excellent mother. No doubt John would have had a good life.’

'From what Dean tells me, he did. He joined the Army for a while. Before everything happened with Azazel, he had a good life. And that was apparently all foretold, so not a lot we could have done to change it.’ You followed Dean as he turned off into a motel parking lot. A frown graced your face. 'Looks like the boys need a pit stop. We should be okay for a few hours. She’s not gonna catch up to us that quickly.’

'You are…confident.’ Henry said, as you pulled the car to a stop beside the Impala. 'It is a…good attribute.’

'Thanks. I guess.’ You climbed from the car, looking over at Dean. 'You think we’re gonna be good for a while.’

'Well, I’m starving. We’ve been running all day.’ Dean replied gruffly. 'Couple of hours shut eye won’t get us killed.’

*****

Sleep evaded you. Dean and Sam had gone to a bar for a couple drinks, no doubt to talk about what was going on, and whilst you would normally be involved in that conversation, you’d been volunteered for babysitting duty with granddaddy Winchester. Who was currently sat on a chair flicking through television channels and marvelling at the technology of today.

'This is pretty fascinating.’ He said, and you sat up from the bed you were on, rubbing a hand over your face.

'That’s Oprah. She’s a pretty big deal I guess.’ You crawled from the covers, sitting on the edge of the bed, watching him closely. 'I thought they had televisions in the fifties.’

'Oh we did. Not this advanced though. I saw a show advertised earlier about space. I’ve never seen such things. Do they actually go into space to film it?’

You laughed, shaking your head. 'No. It’s all computer special effects.’

'Really?’ He seemed shocked. 'That’s amazing.’

'I guess.’ You stood up, moving to grab your bag. 'Well, seeing as I’m not going to sleep any time soon, and you seem pretty wired, I’m gonna introduce you to a classic.’ You rooted around in the rucksack before pulling out a DVD. You handed it to Henry and he frowned. 'It’s a film.’

'Films are…this small?’ He flipped the case over in his hand, reading the words on the cover. 'Harry Potter and the Sorcerer’s Stone.’ He looked up, raising an eyebrow. 'It is a film about magic?’

'Yeah. Trust me, you’ll like it.’ You didn’t mention the fact that the boys hated the film and you hadn’t been able to watch it for a while. Taking the case from him, you moved over to the television set, and slipped the disc into the player at the bottom. Henry shifted in the wooden chair, and you shook your head. 'You need to be comfy to watch this.’ You took a seat on the bed and patted the mattress next to you. Henry frowned again, then moved to take the spot next to you.

A hour later, you were slouched against the headboard, watching him with a smile on your face as he lent forward, absorbing every single detail on the screen. His suit jacket had been discarded to the neighbouring bed.

'This is amazing.’ He said quietly, his hand gripping your leg at the scene with Fluffy. 'These things are…not real?’

'No. Completely computer generated.’ Henry turned at your words.

'Computers do this? They must be as big as countries.’ He marvelled and you chuckled.

'Oh god, you’re adorkable.’

A eyebrow raised in your direction and you realised you’d spoken out loud. Your cheeks flushed red as Henry turned to you fully, watching you like he had been the film.

'What does that mean? I’ve never heard that word before.’

You stuttered, shifting on the bed uncomfortably. 'It’s just…a term of affection. A play on another word.’

He thought for a second, then smiled. 'Adorable.’ He nodded. 'You are adorkable too.’ Was it even possible for you to be this red? You felt like your skin was on fire under the inspection of the man before you.

'B-but…you’re married.’

Henry nodded. 'Fifty years ago I was. But my wife is dead, and it wasn’t…my marriage was more of convenience than…’ He seemed a little embarrassed. 'Maisie was a lovely woman. She was beautiful and kind and any man would have been lucky to have someone like that but our relationship was…difficult.’

'Oh. Sorry.’ You didn’t know what else to say.

'It’s been a long time, chronologically anyway, since a woman has intrigued me like you have. You are so different from women in my time. Strong, brave…a hunter!’ He leaned forward. 'And beautiful. You don’t feel the need to adorn yourself with all the powders and rouge. You are simply…astounding.’

You didn’t even realise you’d been holding your breath until it escaped from your lips. 'Wow.’

'Forgive me.’ He reached over, cupping your face with one warm hand. 'But I am captivated by you.’

You couldn’t deny that there was an attraction there. Your brain didn’t even register that technically this guy was like, ninety. Or your best friend’s grandfather.

All your brain could register was that Henry’s lips were moving closer to your own, and you didn’t stop him when they pressed against yours, insistent and probing, tasting you. You moaned against him, your fingers curling into his shoulders without being told to, until he pulled away.

'This is improper.’ He said.

'Yet somehow, not caring.’ You replied, kissing him this time, pulling him closer. The pair of you toppled to the bed, limbs entangled, hands exploring, mouths fused together. His arousal was making itself known against your jean-clad thigh and you arched up against him, dry humping him for all you were worth. He grunted into your mouth, his hand sliding up underneath your top to cup your breast through your bra.

You paused, pushing him off enough to remove your top, and Henry took the hint, pulling off his own top before throwing it onto the other bed to join his blazer. You weren’t so tidy, throwing your top to the floor, your bra quickly following. When you were both topless, he pulled you back against him, and you revelled in the feel of his bare chest against your sensitive nipples, his fingers roaming your skin to twist and pinch in all the right spots. Your hands scratched at his chest, moving down to his pants, your fingers deftly undoing the button to allow his erection more space within the confines of the material. Sliding inside, you grasped him through his cotton underwear and he groaned against you.

'You are so forward.’ He whispered and you couldn’t help the smile on your face at his words. Not exactly dirty talk but…yeah, you were.

'It gets better.’ You replied, keeping hold of his cock as you pushed him up, using your free hand to work his pants down to his mid-thigh, freeing his manhood entirely. Leaning down, you licked his tip, and his hips jerked forward, a gasp tearing itself from his mouth.

'Oh.’

Not the most manly sound you’d ever heard, but it worked. Obviously Henry Winchester had never had a blow job before. And that only prompted you to go to town. You licked the length of him, one hand gripping him at the base and the other fondling his balls. He was practically shaking by the time you slipped your lips over him, letting the head of his cock punch at the back of your throat as you fucked him with your mouth.

His hands moved, sliding through your hair as you sucked his dick, his head thrown back and lips parted in a “o” of pleasure. You didn’t stop, closing your eyes as you grinding your own hips against the mattress in response to his bliss.

'I’m going to…’ He warned, his hips pistoning forward and you stopped, pulling away to look up at him, wiping away excess saliva from your mouth. Henry looked down at you, eyes darkened with arousal, and then you saw the real Winchester in him. That dark, dangerous edge, the out of control aspect that you were used to seeing in the boys on a hunt, and it only made you want him more.

Henry, apparently, had the same idea. He pounced on you, pulling your pants down your legs to discard them on the floor, his need too great to care about propriety as he threw his own to join them. He kissed you hard, his cock bouncing against your thigh, leaving a trail of pre-cum as he thrust against you. His lips left yours, seeking out your breasts, suckling on one hard nipple and then the other, leaving you a panting, wanton mess underneath him.

'Henry…’ You gasped, gripping his head between your hands as he reached down to grab his cock, positioning himself at your entrance. With one single thrust, he was inside you, buried to the hilt, and you cried out, bucking your hips up into him. Henry’s hands held you in place as he tried to map out your entire body underneath his, and you held on when he started to move, his cock dragging back from your tight walls before slamming back into you.

'Fuck -’ He swore and your eyes widened at his use of the curse. 'You are so…perfect.’ He bent his head, sucking at your right nipple, his hips keeping a strong pace as he fucked you into the motel mattress. Releasing your breast, he moved to kiss you again, his arms sliding underneath you to hold you tightly against him, allowing only for the movement of his thrusts into you as he fucked you. 'So perfect.’ He captured you in a deep kiss, his tongue almost mimicking the pounding of his cock, sending you into a spiralled haze of bliss. Your orgasm was swift in approaching and crashed over you like a wave, your cries swallowed by his mouth, his grunts swallowed by yours as his cock swelled and pulsed, before he painted your walls with his thick, warm cum.

He kept kissing you as he rode out his orgasm, coaxing every drop of pleasure from your body before he stopped moving entirely, pressing one last kiss to your forehead before releasing you.

'That was…’ You whispered, unable to finish the sentence. Henry smiled.

'Amazing.’ He agreed. 'Maybe not the best idea, but the moment I saw you…’ He blushed, withdrawing from your body. 'We should probably clean up.’

'Yeah. I doubt the boys would be too happy to find out that…’ You’d fucked their grandad? 'This happened.’

'Agreed.’ He smiled, picking up his discarded pants. 'We shall keep this between us?’

You nodded. Somehow, you were perfectly fine with that.


End file.
